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    Tizanidine HCl

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

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    2D Structure
    Also known as: Tizanidine hcl, 64461-82-1, Zanaflex, Tizanidine (hydrochloride), 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine hydrochloride, Ds 103-282
    Molecular Formula
    C9H9Cl2N5S
    Molecular Weight
    290.17  g/mol
    InChI Key
    ZWUKMNZJRDGCTQ-UHFFFAOYSA-N
    FDA UNII
    B53E3NMY5C
    Tizanidine Hydrochloride is the hydrochloride salt form of tizanidine, an imidazoline derivative structurally similar to clonidine and an adrenergic agonist with muscle relaxant property. Tizanidine stimulates alpha-2 adrenergic receptors in the central nervous system, thereby inhibiting presynaptic release of norepinephrine and increasing the inhibitory effect on alpha motor neurons and motor reflexes. Tizanidine exerts some activity at the postsynaptic excitatory amino acid receptors and imidazoline receptors which may contribute to the overall reduction in facilitation of spinal motor neurons. Overall, tizanidine hydrochloride causes muscle relaxation, reduces spasticity and antinociceptive effects.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-chloro-N-(4,5-dihydro-1H-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine;hydrochloride
    2.1.2 InChI
    InChI=1S/C9H8ClN5S.ClH/c10-5-1-2-6-8(15-16-14-6)7(5)13-9-11-3-4-12-9;/h1-2H,3-4H2,(H2,11,12,13);1H
    2.1.3 InChI Key
    ZWUKMNZJRDGCTQ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1CN=C(N1)NC2=C(C=CC3=NSN=C32)Cl.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    B53E3NMY5C
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 5-chloro-4-(2-imidazolin-2-yl-amino)-2,1,3-benzothiadiazole

    2. Ds 103-282

    3. Sirdalud

    4. Tizanidine

    5. Tizanidine Monohydrochloride

    6. Zanaflex

    2.3.2 Depositor-Supplied Synonyms

    1. Tizanidine Hcl

    2. 64461-82-1

    3. Zanaflex

    4. Tizanidine (hydrochloride)

    5. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine Hydrochloride

    6. Ds 103-282

    7. An021

    8. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)benzo[c][1,2,5]thiadiazol-4-amine Hydrochloride

    9. B53e3nmy5c

    10. Tizanidine (as Hydrochloride)

    11. 5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole Monohydrochloride

    12. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine;hydrochloride

    13. Ds-103-282

    14. 5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole Hydrochloride

    15. An-021

    16. 64461-82-1 (hcl)

    17. 2,1,3-benzothiadiazol-4-amine, 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-, Monohydrochloride

    18. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazole-4-amine Hydrochloride

    19. Smr000499584

    20. Unii-b53e3nmy5c

    21. Sr-01000765392

    22. Tizanidine * Hcl

    23. Zanaflex (tn)

    24. Mfcd00798231

    25. Tizanidine Hydrochloride [usan:usp:jan]

    26. 5-iodoisoquinolin-8-ol

    27. Schembl41199

    28. Mls001076686

    29. Mls001306412

    30. Mls001333593

    31. Chebi:9609

    32. Tizanidine Hydrochloride- Bio-x

    33. Chembl1200329

    34. Dtxsid9046990

    35. Ds-103282 Ch

    36. Hy-b0194a

    37. An-021a

    38. Nvd-422

    39. Amy18121

    40. Bcp28540

    41. Tox21_501114

    42. S1437

    43. Tizanidine Hydrochloride [mi]

    44. Tizanidine Hydrochloride (jp17/usp)

    45. Tizanidine Hydrochloride [jan]

    46. Akos005267234

    47. Brn0618691

    48. Ccg-220602

    49. Ccg-222418

    50. Ks-1120

    51. Lp01114

    52. Nc00654

    53. Tizanidine Hydrochloride [usan]

    54. Tizanidine Hydrochloride [mart.]

    55. Tizanidine Hydrochloride [vandf]

    56. Ncgc00261799-01

    57. Tizanidine Hydrochloride [who-dd]

    58. Ac-22546

    59. Bt164478

    60. Db-011661

    61. Ds-103282

    62. Ds103-282

    63. Ft-0656022

    64. Sw199068-2

    65. T2527

    66. En300-49853

    67. Tizanidine Hydrochloride [orange Book]

    68. D00776

    69. D70434

    70. Tizanidine Hydrochloride [ep Monograph]

    71. Tizanidine Hydrochloride [usp Impurity]

    72. Tizanidine Hydrochloride [usp Monograph]

    73. Tizanidine Hydrochloride, >=98% (hplc), Powder

    74. Sr-01000765392-4

    75. Q27274381

    76. Tizanidine Hydrochloride 100 Microg/ml In Acetonitrile

    77. 5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazolehydrochloride

    78. Tizanidine Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    79. (5-chloro-2,1,3-benzothiadiazol-4-yl)-(4,5-dihydro-1h-imidazol-2-yl)azanium;chloride

    80. 5-(chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3-benzothiadiazol-4-amine Hydrochloride

    81. 5-chloro-4-(2-imidazolin-2-ylamino)-2,1,3-benzothiadiazole Monohydrochloride.

    82. 5-chloro-4-[(4,5-dihydro-1h-imidazol-2-yl)amino]-2,1,3-benzothiadiazole Hydrochloride

    83. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)-2,1,3benzothiadiazole-4-amine Hydrochloride

    84. 5-chloro-n-(4,5-dihydro-1h-imidazol-2-yl)benzo[c][1,2,5]thiadiazol-4-aminehydrochloride

    85. Tizanidine Hydrochloride, 500 Mug/ml In Methanol, Certified Reference Material

    86. Tizanidine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 290.17 g/mol
    Molecular Formula C9H9Cl2N5S
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count2
    Exact Mass288.9955719 g/mol
    Monoisotopic Mass288.9955719 g/mol
    Topological Polar Surface Area90.4 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity300
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameTizanidine hydrochloride
    PubMed HealthTizanidine (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelZanaflex (tizanidine hydrochloride) is a centrally acting 2-adrenergic agonist. Tizanidine HCl (tizanidine) is a white to off-white, fine crystalline powder, which is odorless or with a faint characteristic odor. Tizanidine is slightly soluble in...
    Active IngredientTizanidine hydrochloride
    Dosage FormTablet; Capsule
    RouteOral
    Strengtheq 4mg base; eq 2mg base; eq 6mg base
    Market StatusPrescription
    CompanyCorepharma; Mylan Pharms; Teva; Apotex; Sun Pharm Inds; Prosam Labs; Sandoz; Dr Reddys Labs; Mylan; Unichem Labs

    2 of 4  
    Drug NameZanaflex
    Drug LabelZanaflex (tizanidine hydrochloride) is a centrally acting 2-adrenergic agonist. Tizanidine HCl (tizanidine) is a white to off-white, fine crystalline powder, which is odorless or with a faint characteristic odor. Tizanidine is slightly soluble in...
    Active IngredientTizanidine hydrochloride
    Dosage FormTablet; Capsule
    RouteOral
    Strengtheq 4mg base; eq 2mg base; eq 6mg base
    Market StatusPrescription
    CompanyAcorda

    3 of 4  
    Drug NameTizanidine hydrochloride
    PubMed HealthTizanidine (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelZanaflex (tizanidine hydrochloride) is a centrally acting 2-adrenergic agonist. Tizanidine HCl (tizanidine) is a white to off-white, fine crystalline powder, which is odorless or with a faint characteristic odor. Tizanidine is slightly soluble in...
    Active IngredientTizanidine hydrochloride
    Dosage FormTablet; Capsule
    RouteOral
    Strengtheq 4mg base; eq 2mg base; eq 6mg base
    Market StatusPrescription
    CompanyCorepharma; Mylan Pharms; Teva; Apotex; Sun Pharm Inds; Prosam Labs; Sandoz; Dr Reddys Labs; Mylan; Unichem Labs

    4 of 4  
    Drug NameZanaflex
    Drug LabelZanaflex (tizanidine hydrochloride) is a centrally acting 2-adrenergic agonist. Tizanidine HCl (tizanidine) is a white to off-white, fine crystalline powder, which is odorless or with a faint characteristic odor. Tizanidine is slightly soluble in...
    Active IngredientTizanidine hydrochloride
    Dosage FormTablet; Capsule
    RouteOral
    Strengtheq 4mg base; eq 2mg base; eq 6mg base
    Market StatusPrescription
    CompanyAcorda

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Muscle Relaxants, Central

    A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358) (See all compounds classified as Muscle Relaxants, Central.)

    Parasympatholytics

    Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)

    Analgesics

    Compounds capable of relieving pain without the loss of CONSCIOUSNESS. (See all compounds classified as Analgesics.)

    Anticonvulsants

    Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

    Adrenergic alpha-2 Receptor Agonists

    Compounds that bind to and activate ADRENERGIC ALPHA-2 RECEPTORS. (See all compounds classified as Adrenergic alpha-2 Receptor Agonists.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Central alpha-2 Adrenergic Agonist [EPC]; Adrenergic alpha2-Agonists [MoA]